(3S)-3,8-Di­bromo-4-phenyl-2,3-di­hydro-1H-1,5-benzodi­aza­pin-2-one

Essaghouani, A.; Boulhaoua, M.; Lahmidi, S.; Mohamed Abdelahi, M.M.; Essassi, E.M.; Mague, J.T.

doi:10.1107/S2414314617003893

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 3| March 2017| x170389

https://doi.org/10.1107/S2414314617003893

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(3S)-3,8-Dibromo-4-phenyl-2,3-dihydro-1H-1,5-benzodiazapin-2-one

Abdelhanine Essaghouani,^a ^* Mohammed Boulhaoua,^a Sanae Lahmidi,^a Mohamed Mokhtar Mohamed Abdelahi,^a El Mokhtar Essassi ^a and Joel T. Mague ^b

^aLaboratoire de Chimie Organique Hétérocyclique, URAC 21, Pôle de Compétence Pharmacochimie, Av Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, Morocco, and ^bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
^*Correspondence e-mail: essaghouani.hanine@gmail.com

Edited by S. Bernès, Benemérita Universidad Autónoma de Puebla, México (Received 18 December 2016; accepted 9 March 2017; online 24 March 2017)

In the title compound, C₁₅H₁₀Br₂N₂O, one Br atom is disordered over two non-chemically equivalent sites, and as a consequence, the crystallized sample contains a mixture of isomers, viz. 98.4% of 3,8-dibromo-4-phenyl-2,3-dihydro-1H-1,5-benzodiazapin-2-one and 1.6% of 3,6-dibromo-4-phenyl-2,3-dihydro-1H-1,5-benzodiazapin-2-one. The seven-membered ring adopts a boat conformation. In the crystal, pairwise N—H⋯O hydrogen bonds form centrosymmetric dimers, which are associated in the crystal through a combination of π–π stacking and C—H⋯π(ring) interactions.

Keywords: crystal structure; benzodiazepine; hydrogen bonding; π-stacking.

CCDC reference: 1537047

Structure description

Recently there has been considerable interest in the chemistry of 1,5-benzodiazepines. This is undoubtedly due to their broad variety of biological functions such as antidepressant (Basawaraj et al., 2008 ), anti-inflammatory (Ha et al., 2010 ), and antihelmintic activities (Kumar & Joshi, 2008 ). As a continuation of our studies of new 1,5-benzodiazepin-2-one derivatives (Essaghouani et al., 2016 ), we report here on the synthesis and structure of the title compound (Fig. 1).

Figure 1
The title molecule with labelling scheme and 50% probability ellipsoids. Only the main isomer is represented.

The seven-membered ring adopts a boat conformation with the Br2 substituent in axial position. A Cremer–Pople puckering analysis of this conformation yielded the parameters q₂ = 0.711 (2), q₃ = 0.177 (2) Å, φ₂ = 202.1 (2) and φ₃ = 309.7 (7)°.

In the crystal, the molecules form dimers through N2—H2A⋯O1ⁱ [symmetry code: (i) −x, 1 − y, −z] hydrogen bonds (Table 1 and Fig. 2). These units are further associated by a combination of a π–π-stacking interaction between the C10–C15 ring and its counterpart at position 2 − x, 2 − y, 1 − z [centroid-to-centroid distance: 3.592 (2) Å; slippage: 0.95 Å] and a C4—H4⋯π(ring) interaction with the C10–C15 ring at x, −1 + y, z to form a three-dimensional network structure (Table 1, Figs. 2 and 3).

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C10–C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1ⁱ	0.88	1.99	2.842 (2)	164
C4—H4⋯Cg1ⁱⁱ	0.95	0.96	3.824 (3)	151
Symmetry codes: (i) -x, -y+1, -z; (ii) x, y-1, z.

Figure 2
Detail of the N—H⋯O hydrogen bonding (blue dotted lines), π–π-stacking (purple dotted line) and C—H⋯π(ring) (black dotted line) interactions. [Symmetry codes: (i) −x, 1 − y, −z; (ii) 2 − x, 2 − y, 1 − z; (iii) x, −1 + y, z].

Figure 3
The packing viewed along the a axis.

It appears from the final structure refinement that an impurity was present in the crystal (ca 1.6% of the crystal content) which, from trial refinements, was found to be an isomer of the title compound with bromine attached to C5 instead of C3. Inclusion of the alternate location of Br1 together with the constraint of the total occupancy of disordered sites to unity improved the final refinement.

Synthesis and crystallization

A mixture of 4-phenyl-2,3-dihydro-1H-l,5-benzodiazepin-2-one (2.36 g, 10 mmol) and N-bromosuccinimide (3.55 g, 20 mmol) in anhydrous CHCl₃ (40 ml) was refluxed for 6 h. After cooling, the succinimide crystals formed were removed by filtration. The filtrate was evaporated under reduced pressure. The resulting residue was purified by column chromatography (EtOAc/hexane 1/9), to afford the title compound as pale-yellow crystals (yield: 45%).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. In the final stages of the refinement the largest residual peak appeared about 1.7 Å from C5 and in the plane of the C1–C6 ring. Based on trial refinements, this residual was assigned to an alternate location of Br1 with a small occupancy factor. The refinement of this occupancy for the minor isomer converged to 0.0159 (7), while the major isomer contributes to the structure factors with an occupancy of 0.9841 (7).

Table 2
Experimental details

Crystal data
Chemical formula	C₁₅H₁₀Br₂N₂O
M_r	394.07
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	100
a, b, c (Å)	7.8931 (8), 9.9295 (10), 10.2411 (11)
α, β, γ (°)	101.751 (1), 105.968 (2), 109.482 (1)
V (Å³)	687.77 (12)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	5.89
Crystal size (mm)	0.35 × 0.31 × 0.12

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.39, 0.54
No. of measured, independent and observed [I > 2σ(I)] reflections	13311, 3674, 3263
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.688

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.073, 1.07
No. of reflections	3674
No. of parameters	185
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.60, −0.70
Computer programs: APEX3 and SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015a ), SHELXL2014/7 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1537047

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314617003893/bh4023sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617003893/bh4023Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617003893/bh4023Isup3.cdx

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(3S)-3,8-Dibromo-4-phenyl-2,3-dihydro-1H-1,5-benzodiazapin-2-one top

Crystal data top

C₁₅H₁₀Br₂N₂O	Z = 2
M_r = 394.07	F(000) = 384
Triclinic, P1	D_x = 1.903 Mg m⁻³
a = 7.8931 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.9295 (10) Å	Cell parameters from 8714 reflections
c = 10.2411 (11) Å	θ = 2.2–29.3°
α = 101.751 (1)°	µ = 5.89 mm⁻¹
β = 105.968 (2)°	T = 100 K
γ = 109.482 (1)°	Thick plate, light yellow
V = 687.77 (12) Å³	0.35 × 0.31 × 0.12 mm

Data collection top

Bruker SMART APEX CCD diffractometer	3674 independent reflections
Radiation source: fine-focus sealed tube	3263 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 8.3333 pixels mm^-1	θ_max = 29.3°, θ_min = 2.2°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −13→13
T_min = 0.39, T_max = 0.54	l = −14→14
13311 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.028	Hydrogen site location: mixed
wR(F²) = 0.073	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.037P)² + 0.8581P] where P = (F_o² + 2F_c²)/3
3674 reflections	(Δ/σ)_max = 0.001
185 parameters	Δρ_max = 1.60 e Å⁻³
1 restraint	Δρ_min = −0.70 e Å⁻³

Special details top

Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, collected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = –30.00 and 210.00°. The scan time was 10 sec/frame.

Refinement. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.98 Å) while those attached to nitrogen were placed in locations derived from a difference map and their coordinates adjusted to give N—H = 0.88 %A. All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms. In the final stages of the refinement, a noticeable peak remained about 1.7 Å from C5 while U_iso for Br1 was distinctly larger than that of Br2. These suggested a small presence of the isomer with Br on C5 instead of C3 and refinement of this model with restraints to make the geometries of the two components comparable led to a ca. 1.4% contribution by the minor isomer.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Br1A	0.30208 (3)	−0.00789 (2)	0.10256 (3)	0.02206 (8)	0.9841 (7)
Br1B	0.9623 (7)	0.4998 (15)	0.2875 (17)	0.02206 (8)	0.0159 (7)
Br2	0.43259 (3)	0.63603 (3)	0.45110 (2)	0.01890 (7)
O1	0.1287 (2)	0.67702 (18)	0.1270 (2)	0.0219 (4)
N1	0.6794 (3)	0.6709 (2)	0.2233 (2)	0.0152 (4)
N2	0.2434 (3)	0.4979 (2)	0.0929 (2)	0.0148 (4)
H2A	0.1409	0.4450	0.0133	0.018*
C1	0.3751 (3)	0.4317 (2)	0.1289 (2)	0.0136 (4)
C2	0.2943 (3)	0.2749 (2)	0.0982 (2)	0.0146 (4)
H2	0.1578	0.2193	0.0569	0.018*
C3	0.4140 (3)	0.2009 (2)	0.1283 (2)	0.0167 (4)
H3B	0.3576	0.0941	0.1119	0.020*	0.0159 (7)
C4	0.6151 (4)	0.2789 (3)	0.1822 (3)	0.0198 (5)
H4	0.6967	0.2275	0.2005	0.024*
C5	0.6922 (3)	0.4333 (3)	0.2082 (3)	0.0186 (4)
H5A	0.8295	0.4818	0.2423	0.022*	0.9841 (7)
C6	0.5768 (3)	0.5141 (2)	0.1870 (2)	0.0143 (4)
C7	0.6228 (3)	0.7685 (2)	0.2771 (2)	0.0138 (4)
C8	0.4336 (3)	0.7311 (2)	0.3006 (2)	0.0147 (4)
H8	0.4231	0.8285	0.3353	0.018*
C9	0.2562 (3)	0.6318 (2)	0.1656 (3)	0.0153 (4)
C10	0.7556 (3)	0.9317 (2)	0.3269 (2)	0.0153 (4)
C11	0.7572 (4)	1.0337 (3)	0.4444 (3)	0.0255 (5)
H11	0.6653	1.0001	0.4872	0.031*
C12	0.8911 (4)	1.1833 (3)	0.4991 (3)	0.0300 (6)
H12	0.8938	1.2508	0.5809	0.036*
C13	1.0218 (4)	1.2339 (3)	0.4332 (3)	0.0258 (6)
H13	1.1106	1.3370	0.4676	0.031*
C14	1.0214 (4)	1.1344 (3)	0.3188 (3)	0.0293 (6)
H14	1.1111	1.1688	0.2745	0.035*
C15	0.8906 (4)	0.9830 (3)	0.2666 (3)	0.0267 (5)
H15	0.8944	0.9147	0.1888	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1A	0.02331 (13)	0.01058 (11)	0.02899 (14)	0.00794 (9)	0.00466 (10)	0.00528 (9)
Br1B	0.02331 (13)	0.01058 (11)	0.02899 (14)	0.00794 (9)	0.00466 (10)	0.00528 (9)
Br2	0.01833 (12)	0.02158 (12)	0.01888 (12)	0.00794 (9)	0.00865 (9)	0.00892 (9)
O1	0.0149 (8)	0.0127 (7)	0.0306 (10)	0.0059 (6)	−0.0009 (7)	0.0046 (7)
N1	0.0135 (8)	0.0149 (9)	0.0142 (9)	0.0041 (7)	0.0038 (7)	0.0039 (7)
N2	0.0124 (8)	0.0118 (8)	0.0155 (9)	0.0041 (7)	0.0000 (7)	0.0035 (7)
C1	0.0146 (10)	0.0135 (9)	0.0129 (10)	0.0071 (8)	0.0040 (8)	0.0038 (8)
C2	0.0163 (10)	0.0117 (9)	0.0139 (10)	0.0052 (8)	0.0046 (8)	0.0027 (8)
C3	0.0215 (11)	0.0115 (9)	0.0153 (10)	0.0067 (8)	0.0057 (9)	0.0027 (8)
C4	0.0213 (11)	0.0180 (11)	0.0200 (11)	0.0120 (9)	0.0053 (9)	0.0025 (9)
C5	0.0151 (10)	0.0186 (11)	0.0208 (11)	0.0082 (9)	0.0062 (9)	0.0027 (9)
C6	0.0152 (10)	0.0140 (10)	0.0126 (10)	0.0052 (8)	0.0057 (8)	0.0026 (8)
C7	0.0126 (10)	0.0129 (9)	0.0134 (10)	0.0036 (8)	0.0029 (8)	0.0051 (8)
C8	0.0142 (10)	0.0113 (9)	0.0161 (10)	0.0048 (8)	0.0034 (8)	0.0034 (8)
C9	0.0112 (9)	0.0119 (9)	0.0196 (11)	0.0024 (8)	0.0034 (8)	0.0063 (8)
C10	0.0126 (10)	0.0122 (9)	0.0172 (10)	0.0037 (8)	0.0009 (8)	0.0055 (8)
C11	0.0166 (11)	0.0168 (11)	0.0369 (15)	0.0050 (9)	0.0098 (11)	0.0000 (10)
C12	0.0178 (12)	0.0178 (12)	0.0432 (16)	0.0058 (9)	0.0070 (11)	−0.0039 (11)
C13	0.0175 (11)	0.0129 (10)	0.0335 (14)	0.0010 (9)	−0.0037 (10)	0.0079 (10)
C14	0.0275 (14)	0.0253 (13)	0.0238 (13)	−0.0027 (10)	0.0081 (11)	0.0104 (10)
C15	0.0287 (14)	0.0231 (12)	0.0171 (12)	0.0003 (10)	0.0087 (10)	0.0020 (9)

Geometric parameters (Å, º) top

Br1A—C3	1.891 (2)	C5—C6	1.404 (3)
Br1B—C5	1.879 (4)	C5—H5A	0.9503
Br2—C8	1.964 (2)	C7—C10	1.490 (3)
O1—C9	1.235 (3)	C7—C8	1.513 (3)
N1—C7	1.284 (3)	C8—C9	1.518 (3)
N1—C6	1.406 (3)	C8—H8	1.0000
N2—C9	1.342 (3)	C10—C15	1.381 (3)
N2—C1	1.411 (3)	C10—C11	1.401 (3)
N2—H2A	0.8800	C11—C12	1.387 (3)
C1—C2	1.398 (3)	C11—H11	0.9500
C1—C6	1.403 (3)	C12—C13	1.396 (4)
C2—C3	1.387 (3)	C12—H12	0.9500
C2—H2	0.9500	C13—C14	1.369 (4)
C3—C4	1.395 (3)	C13—H13	0.9500
C3—H3B	0.9600	C14—C15	1.394 (4)
C4—C5	1.383 (3)	C14—H14	0.9500
C4—H4	0.9500	C15—H15	0.9500

C7—N1—C6	123.5 (2)	C10—C7—C8	116.56 (19)
C9—N2—C1	127.68 (19)	C7—C8—C9	113.84 (19)
C9—N2—H2A	116.2	C7—C8—Br2	110.89 (14)
C1—N2—H2A	116.1	C9—C8—Br2	109.57 (14)
C2—C1—C6	120.4 (2)	C7—C8—H8	107.4
C2—C1—N2	116.27 (19)	C9—C8—H8	107.4
C6—C1—N2	123.30 (19)	Br2—C8—H8	107.4
C3—C2—C1	119.8 (2)	O1—C9—N2	122.4 (2)
C3—C2—H2	120.1	O1—C9—C8	118.9 (2)
C1—C2—H2	120.1	N2—C9—C8	118.69 (19)
C2—C3—C4	121.1 (2)	C15—C10—C11	118.5 (2)
C2—C3—Br1A	119.18 (17)	C15—C10—C7	120.8 (2)
C4—C3—Br1A	119.64 (17)	C11—C10—C7	120.4 (2)
C2—C3—H3B	119.4	C12—C11—C10	120.9 (2)
C4—C3—H3B	119.4	C12—C11—H11	119.6
C5—C4—C3	118.1 (2)	C10—C11—H11	119.6
C5—C4—H4	120.9	C11—C12—C13	119.5 (3)
C3—C4—H4	120.9	C11—C12—H12	120.2
C4—C5—C6	122.7 (2)	C13—C12—H12	120.2
C4—C5—Br1B	106.1 (4)	C14—C13—C12	119.8 (2)
C6—C5—Br1B	131.0 (5)	C14—C13—H13	120.1
C4—C5—H5A	115.6	C12—C13—H13	120.1
C6—C5—H5A	121.8	C13—C14—C15	120.7 (3)
C1—C6—C5	117.7 (2)	C13—C14—H14	119.7
C1—C6—N1	127.2 (2)	C15—C14—H14	119.7
C5—C6—N1	115.1 (2)	C10—C15—C14	120.6 (2)
N1—C7—C10	118.3 (2)	C10—C15—H15	119.7
N1—C7—C8	125.11 (19)	C14—C15—H15	119.7

C9—N2—C1—C2	143.1 (2)	N1—C7—C8—C9	−56.2 (3)
C9—N2—C1—C6	−39.4 (3)	C10—C7—C8—C9	126.7 (2)
C6—C1—C2—C3	1.4 (3)	N1—C7—C8—Br2	67.9 (3)
N2—C1—C2—C3	179.0 (2)	C10—C7—C8—Br2	−109.17 (18)
C1—C2—C3—C4	−3.3 (3)	C1—N2—C9—O1	−177.4 (2)
C1—C2—C3—Br1A	174.27 (17)	C1—N2—C9—C8	2.4 (3)
C2—C3—C4—C5	1.6 (4)	C7—C8—C9—O1	−123.5 (2)
Br1A—C3—C4—C5	−176.00 (18)	Br2—C8—C9—O1	111.7 (2)
C3—C4—C5—C6	2.1 (4)	C7—C8—C9—N2	56.7 (3)
C3—C4—C5—Br1B	177.3 (6)	Br2—C8—C9—N2	−68.1 (2)
C2—C1—C6—C5	2.1 (3)	N1—C7—C10—C15	27.1 (3)
N2—C1—C6—C5	−175.4 (2)	C8—C7—C10—C15	−155.6 (2)
C2—C1—C6—N1	179.9 (2)	N1—C7—C10—C11	−147.3 (2)
N2—C1—C6—N1	2.5 (4)	C8—C7—C10—C11	30.0 (3)
C4—C5—C6—C1	−3.9 (4)	C15—C10—C11—C12	0.1 (4)
Br1B—C5—C6—C1	−177.7 (7)	C7—C10—C11—C12	174.6 (2)
C4—C5—C6—N1	178.0 (2)	C10—C11—C12—C13	2.2 (4)
Br1B—C5—C6—N1	4.2 (8)	C11—C12—C13—C14	−2.5 (4)
C7—N1—C6—C1	36.6 (3)	C12—C13—C14—C15	0.5 (4)
C7—N1—C6—C5	−145.5 (2)	C11—C10—C15—C14	−2.0 (4)
C6—N1—C7—C10	172.9 (2)	C7—C10—C15—C14	−176.6 (2)
C6—N1—C7—C8	−4.2 (3)	C13—C14—C15—C10	1.8 (4)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C10–C15 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.88	1.99	2.842 (2)	164
C4—H4···Cg1ⁱⁱ	0.95	0.96	3.824 (3)	151

Symmetry codes: (i) −x, −y+1, −z; (ii) x, y−1, z.

Acknowledgements

JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.

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Volume 2| Part 3| March 2017| x170389

https://doi.org/10.1107/S2414314617003893

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(3S)-3,8-Di­bromo-4-phenyl-2,3-di­hydro-1H-1,5-benzodi­aza­pin-2-one

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds

(3S)-3,8-Dibromo-4-phenyl-2,3-dihydro-1H-1,5-benzodiazapin-2-one